Oh my god is this one annoying to deal with, especially when it's holding Rocky Helmet. Any tips on how to counter this? It just keeps Roosting to full health while it's low, and then using Whirlwind which makes my Pokemon take damage from Stealth Rock, and whenever I deal damage to it I take just as much damage in return from Rocky Helmet.

I know that this is a old school move from a gen1 and I am playing crystal version on my psp but here is a fighter move set for skarmary but keep in mind this is a non-team affiliated skill set and it's soul purpose is "how long it can last in battle" and "how fast it has become"

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Ability:Sturdy
Evs:252Hp/252Def/4SpDef
Impish Nature
-Spikes
-Stealth rock
-Roost
-Counter(catch skarmory in gen 3 games and teach this from a move tutor in either FRLF)

Okay a bit odd but the point is first you set up entry hazards. You need a total of 4 turns which is completely possible with his defensiveness and roost. After he is done setting up he can always come back and destroy physical attackers with counter. Get hit by a physical move and strike them back and use roost to recover those damages and repeat this process over and over. Prediction is the only problem here but no one will expect a counter from a skarmory.

Erm, like I said, this is a "Stallerish/SrockSpikes dude for your sandstorm team" and "watch out for taunt" - In other words, He isn't meant to be an attacker. (as You can see, I gave him 0 attack Evs)
I would have thrown Sky drop in there for more stalling, but it's banned in competitive battling. :(

Counter is the gimmick to this set. Skarmory can wall Mega Pinsir easily, and if it tries to go for a CC, Skarmory's Counter kills it. Oh, and assuming you have Sturdy intact, wave goodbye to your little Talonflame as Skarmory lives Flare Blitz and one-shots with Counter. Shed Shell is to escape from Magnezone.
Only downside is that if you're trying to get it in-game, you're gonna have to do A LOT of transferring.

-Steel Wing Is STAB + Possible Defense Raise.
-Brave Bird/Drill Peck is STAB. I prefer B-Bird to D-Peck.
-Autotomize or Agility is required for such a slow bird.
-And you can't have an offensive Skarm w/out Swords Dance. (Unless it has a choice Band.)

Nature: Jolly/Adamant (Skarmory needs more Speed and he has no use for Sp Attack, Adamant if you want Attack instead of Speed)

Moves:
Drill Peck (Good Dmg, High Accuracy, STAB + lots of uses)

Steel Wing (Good Dmg, ok Accuracy, STAB + Chance of Defence Boost)

Swords Dance/Autotomise (for attack or Speed Boost depending on what you think you need)

Roost (for healing and remaining Sturdy)

Good and nice Moveset for Skarmory, not exactly the most tactical moveset but good for slaying mostly everything XD, the Leftovers and roost helps keeping the Sturdy intact and helps you to come to Attack/Speed (Swords Dance/Autotomise +8 pretty easy and still remaining at mostly full hp if you do it right.

Stealth Rock and Spikes are there for setting up hazards, and Whirlwind is a possible choice to continuously force your opponent out and bring another back in to get repetitive damage from the hazards. Roost is for healing purposes. If you want damage, you can substitute out Whirlwind for Brave Bird.

Alright, I recently used this Skarmory in a nice Battle Spot Battle and annoyed the other team real bad. So here goes...

Skarmory @ Leftovers
Ability: Sturdy
Nature: Impish
Moves: Toxic, poisoning and wearing other Sturdy Pokemon downSpikes, because any Stall Skarmory has SpikesRoost, to heal and not get SE hit from Electric(but get SE hit from Ground XP) and healingSandstorm, to wear down even more and to make teammate's Sand Rush/Sand Veil be useful...

You can swap Sandstorm for Steel Wing or Aerial Ace (Actually, you're running Roost, so why not Brave Bird?!) if you don't want to be Taunt bait...

Sturdy + Custap Berry enables you to use at least Stealth Rock and one Spikes. After that you have the choice to set up another layer of Spikes, use Whirlwind to damage your opponent one by one or use Iron Head to inflict more damage.

Primarily intended to be used in singles as a toxic wall, though you can lead with it for the Stealth Rock. It's primary purpose is just to use toxic, Brave Birding whenever it has enough feasible HP to spare, and roosting when it doesn't. Stealth Rock deters Fire switch kid but accompanying Pokemon probably need water and ground type moves to beat fire and steel type Pokemon.

Sometimes if you actually don't set Stealth Rock, you get the opportunity to toxic more than one of the enemy team's Pokemon, just remember that Skarmory has limited switch ins due to not being the bulkiest Pokemon around. I find this set fun to use. (Apologies if there's a similar set here already, I couldn't see it.)

I know that this is a old school move from a gen1 and I am playing crystal version on my psp but here is a fighter move set for skarmary but keep in mind this is a non-team affiliated skill set and it's soul purpose is "how long it can last in battle" and "how fast it has become"

Swords Dance + Weak Armor Skarmory! With Swords Dance, Skarmory's already devastating attack is doubled! Brave Bird and Iron Head are for STAB. Although both stab moves aren't very super effective on steel, Skarmory has an extremely powerful coverage move: Rock Smash! To further increase this moves power, Fightinium-Z can be implemented! If not, however, Expert Belt is great for powering up Rock Smash because the only reason you'll ever use it is if it is super effective, given the fact that its base power is way too high. Opponents will expect a Sturdy Skarmory, but they'll regret it if they try to hit it with a physical attack! At the cost of a defense drop, Skarmory's already amazing speed goes through the roof! Then, proceed to sweep entire teams with your +2 attack and +2 speed Skarmory!

Special Attacker Skarmory! Skarmory's insane special attack stat is underestimated for some reason, and I think should be used more often. Flash Cannon and Air Slash are for STAB. Hidden Power Fire can pick off Pokémon like Ferrothorn, Celesteela, and Skarmory. Hidden Power Ground, however, hits Heatran and is also super effective on electric and fire types. Agility can be used to allow Skarmory to outspeed anything, and Roost can restore Life Orb recoil. However, if you don't want to recoil at all, Expert Belt is a phenomenal replacement.